A scalable synthesis of (+)‐coronafacic acid. Issue 4 (30th January 2020)

• Record Type: Journal Article
• Authors: Kato, Nobuki; Miyagawa, Saki; Nomoto, Haruna; Nakayama, Misuzu; Iwashita, Makoto; Ueda, Minoru
• Is Part Of: Chirality. Volume 32:Issue 4(2020)
• Page Start: 423
• Page End: 430
• Publication Date: 2020-01-30
• Subjects: boron‐mediated aldol reaction -- coronafacic acid -- coronatine -- jasmonates -- optical resolution; Chirality -- Periodicals; Pharmaceutical chemistry -- Periodicals; 541.22
• DOI: 10.1002/chir.23172
• Languages: English
• ISSNs: 0899-0042

Abstract

Abstract: A facile, efficient, and scalable synthesis of optically pure coronafacic acid by resolution of racemic coronafacic acid obtained using an improved version of Watson's method has been developed. By optimizing the boron‐mediated aldol reaction of Watson, we were able to prepare 2.1 g of racemic coronafacic acid. This was coupled with (S)‐4‐isopropyl‐2‐oxazolidinone to give a mixture of diastereomeric coronafacyl oxazolidinones, which were readily separable by silica‐gel column chromatography to give 630 mg of optically pure (+)‐coronafacic acid. Abstract :